A recently resurfaced image of Jennifer Aniston and David Letterman has sparked renewed conversations about one of the most uncomfortable moments on The Late Show. The interview, which took place in 2006, featured Aniston promoting her film The Break-Up, a romantic comedy in which she starred alongside Vince Vaughn, who also co-wrote and produced the movie.

From the outset, the interview took an uncomfortable turn as Letterman fixated on Aniston’s legs, offering her repeated compliments throughout their dialogue. Dressed in a black button-down blouse and black shorts, Aniston quickly became the center of Letterman’s admiration. He could not resist praising her legs, prompting the cameraman to zoom in for emphasis. “That’s a tremendous outfit,” he commented, adding, “and the reason that’s a tremendous outfit is because you have tremendous legs. Fantastic legs. You can only wear that if you have lovely, well-shaped, muscular, lengthy legs.”

Aniston, clearly surprised, attempted to downplay the remark, laughing it off by explaining that she had chosen to wear shorts due to the heat. While she consistently maintained her composure, her discomfort was evident during this particular interview, where Letterman seemed overly focused on her legs. Yet, he persisted, returning to the topic with another comment: “Your legs, you’ve got something there.” This exchange left viewers cringing at the time and continues to evoke discomfort today. To add to the awkwardness, he swiftly transitioned to questioning her about her rumored relationships.

In an already tense situation, he swiftly changed the subject and began inquiring about her alleged relationship with Vince Vaughn. Letterman also pressed Aniston on whether it was Vaughn’s suggestion for her to “appear naked in the movie.” Taken aback, Aniston paused before redirecting the question, implying that Letterman should have posed that inquiry to Vaughn during his appearance on the show.

Today, it is widely known that Aniston began dating her co-star Vince Vaughn while they were filming The Break-Up. In a subsequent interview, she disclosed that he played a significant role in her recovery following her highly publicized divorce.

While discussing Vaughn, Letterman could not help but comment on Aniston’s legs. “I can’t get over your legs, I’m telling you. You have something special there,” he remarked. Later in their conversation, he made another remark that seemed to allude to her legs, stating, “I hope to God someone at home is TiVoing this because I can’t stop looking at this shot.” Although it was unclear which shot he was referring to, Aniston’s uncomfortable demeanor indicated that it was yet another emphasis on her legs.

This was not the first instance of Letterman making Aniston visibly uneasy. In a notorious 1998 interview, he grabbed her neck and playfully sucked on a strand of her hair. Aniston, clearly uncomfortable, used a tissue he provided to wipe her hair. He then handed her a tissue to clean off the saliva, further intensifying the awkwardness of the moment.

Aniston managed to navigate the situation with poise, as she has done throughout her career. Renowned for her ability to maintain her composure in challenging circumstances, she successfully kept the conversation flowing. Even after such an uncomfortable encounter, she returned to The Late Show, demonstrating her resilience in overcoming even the most awkward situations.

Two years after her memorable “leg” moments with Letterman, Jennifer Aniston made another appearance on the show, this time donning a stylish pink party dress that once again showcased her remarkable beauty.